Lawesson's reagent → Ethyl 2-thioxopiperidine-4-carboxylate

HRID 62473Notes

Reaction equation

HRID 62473 reaction equation
O=[C:2]1[CH2:7][CH:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:5][CH2:4][NH:3]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:22])=CC=1>C1(C)C=CC=CC=1>[S:22]=[C:2]1[CH2:7][CH:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:5][CH2:4][NH:3]1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 18699051Ethyl 2-oxopiperidine-4-carboxylate

Product 1

HCID 90303563Ethyl 2-thioxopiperidine-4-carboxylateYield 49.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of ethyl 2-oxopiperidine-4-carboxylate (10.76 g, 62.85 mmol) in toluene (120 mL) was added the Lawesson's reagent (25.42 g, 62.85 mmol) under a nitrogen atmosphere. The mixture was heated to reflux for 2 h. Removed the solvent under reduced pressure and the residue was purified by silica gel column chromatography (DCM/EA=20/1) to afford ethyl 2-thioxopiperidine-4-carboxylate (5.8 g, yield 49.3%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 h
  3. customRemoved the solvent under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (DCM/EA=20/1)

Sources & evidence

ORD record
ord-ce5d94626e1349dc8a0e4dace23d5c68
Source dataset
uspto-grants-2016_09
Patent number
US09446130B2

Reaction notes

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